Question
Oxygen pulling on C-H bonds with α-hydrogens, makes it relatively easy to ____ the α-carbon of an aldehyde or ketone.
Answer
Oxygen pulling on C-H bonds with α-hydrogens, makes it relatively easy to deprotonate the α-carbon of an aldehyde or ketone.
Note ↑: The pKa values of aldehyde and ketone -hydrogens range from 16 to 21, much lower than
the pKa values of ethene (44) or ethyne (25), but comparable with those of alcohols (15–18).
Strong bases can therefore remove an -hydrogen. The anions that result are known as
enolate ions or simply enolates.
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____ - carbon is adjacent to the carbonyl carbon.
Through ____, oxygen pulls some of the electron density out of these α-Hydrogens bonded to Carbons, weakening them.
Through induction, oxygen pulls some of the ____ out of these α-Hydrogens bonded to Carbons, weakening them.
Through induction, oxygen pulls some of the electron density out of these α-Hydrogens bonded to Carbons, ____ them.
The ____ of α -hydrogens is augmented by resonance stabilization of the conjugate base.
The acidity of α -hydrogens is augmented by ____.